We just took our big national aesthetics conference virtual. We experimented with all kinds of weird "social sessions" to make Zoom less miserable. Surprise of all surprises - they worked? And people loved them? And they thought it made the community feel real?

A thread:
The surprise hit: the "3 minute nutty talk session". Late night session, Zoom room, people just showed up and improvised a wild 3 minute talk on... anything. Followed by 3 minutes of lightning Q&A. We had talks about the ethics of squirming on Zoom, on the art of movie trailers.
The shocking thing? It was AWESOME. People were in hysterics, going all out with sincere ideas and swinging for the fences. Some of the ideas were silly, some were big but inchoate ideas, some started off tossed off but gathered steam. People said it was the conference highlight.
Backstory: I was Program Chair of the American Society for Aesthetics 2020 Annual Conference - a big, 3-day, 4-track conference. This thing has always been one of the highlights of my year. The aesthetics community is this big, weird, nerdy, loving family of oddball philosophers.
When we realized we had to take it virtual, we thought: we had to do something to give us some little thread of that community. @aaronmeskin volunteered to take charge of a little subcommittee, and we started brainstorming.
I had one single big guiding observation: big Zoom rooms, where a lot of people don't know each other, where you're just supposed to somehow "socialize", are weird awkward failures. So we started trying to figure out ways to not do that.
First, we made parallel social sessions to keep the size down. (For our 300 person conference, we had 3 parallel sessions in each social slot.) My big ideas was: we should try different semi-structured activities.
In each slot, we had one unstructured "cocktail hour". And the other sessions were:

Joke room
Show and tell
Trivia room
3-minute wacky improv talk room
Talent show
I worried these structured rooms would be corny. But they were actually great! Just a little bit of structure I think eases the oddity of trying to figure out who's gonna talk in Zoom. So, in Show and Tell room, people would take turns showing some art object or heirloom
...and then people would pepper them with questions and then all kinds of chat would arise naturally. (Show and Tell may be particularly good for philosophers of art, though, so YMMV).
I also noticed that, in our big unstructured cocktail rooms, the people talking were mostly the well-known senior people. It's really hard to break into an unstructured Zoom chat if you're new to a field, or don't know anybody.
But in the structured activity room, we had tons of junior folks, new folks. And they got to talk, and people got to know them. And it was very clear that new folks to our community were drawn to the structured rooms, and tended to stay there.
This will surprise nobody who knows me but: the idea for structured rooms came from all my recent pandemic experience playing RPGs on Zoom. Again: Zoom socialization is pretty awkward, but the tiny bit of structure provided by RPGs makes it just work.
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